


One Halloween Night

by SolumSam



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Comfort, Crying, First Time, Fluff and Smut, Friends to Lovers, Halloween, Kissing, M/M, Praise Kink, Slow Burn, Smut, Virgin!Castiel, bottom!Castiel, top!dean
Language: English
Status: Completed
Published: 2016-04-25
Updated: 2016-04-25
Packaged: 2018-06-04 09:27:27
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 2,518
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6652342
Author URL: https://archiveofourown.org/users/SolumSam/pseuds/SolumSam
Summary: <blockquote class="userstuff">
              <p>Castiel invites Dean to stay over on Halloween night.</p>
            </blockquote>





	One Halloween Night

Castiel was glad Mary Winchester had let Dean stay the night on Halloween, because it was the perfect time for a scary movie and popcorn with his best friend. The harsh wind rattled against the windows and the lights flickered, causing Cas to curl up beneath the warm blankets. Dean was beside him, his eyes focused on the TV with a small smirk on his face. 

"What's so funny?" Cas whispered, turning to face him. 

Dean's eyes remained on the movie. "The acting," he murmured quietly. "There's obviously something behind her. She just makes it so obvious," he pointed to the screen, and just then, the actress turned. "'S stupid." And there was the monster. 

Cas raised his eyebrows. "Wow." 

Dean sighed softly. "But she's just going to stay there and not do anything, because she's a wuss."

Cas laughed. "How many times have you seen this, Dean?" 

He didn't respond for a moment, but then he turned to look at Cas, staring at his face through the dark room. He shrugged. "Probably eight," he whispered. "But it's okay, because I wanted to watch it with you." His green eyes didn't leave Cas. 

Cas bit his bottom lip, sucking at the soft skin. A few seconds passed before he spoke. "Why are you staring, Dean?" 

Dean smiled. "Am I not allowed to?" 

Castiel swallowed. "I-I-" 

The actress interrupted his thoughts and screamed, causing Cas to look back at the screen. The monster stabbed the girl in the chest, and cheesy fake blood spluttered everywhere. He was going to comment something about the badly-made gore, but Dean's cold hands crept on his cheek, turning him carefully to look back at him. Cas's breath hitched when he saw how close they were. Dean opened his mouth, and Cas could feel his warm breath on his lips. 

"Hey, Cas," he murmured. "Your eyes are really blue." 

Cas nodded slowly. Dean's fingers wrapped around the back of his neck, pulling him even closer. "Your fingers are really cold, Dean," Cas told him, and he chuckled, making his heart race even more. Soon their noses were touching, and the only sound in the room was their breath and the low talking on the TV. "What are you doing, Dean?" 

"I don't know," he replied quietly, and then his lips moved up to Castiel's ear, breathing low and shallow. He paused before nibbling softly at the skin. Cas's breath stopped for a moment. "Is this okay, Cas?" he asked, lowering himself down to Cas's neck and peppering light kisses there. Castiel's breath quickened as Dean's lips opened against his collarbone, his warm mouth lightly sucking on it. 

"W-what," Cas breathed, and Dean's nose trailed back up to his face. His kissed the side of his mouth slowly, then moved down to his jaw. "I-I... " 

"It's alright," Dean whispered against him. "I've got you." Castiel's pulse was so loud he was afraid Dean would hear it and make some snide remark, but he kept quiet, and lightly pushed Cas's shoulder back into the cushion so he was laying down. Dean hovered over him, both hands on either side of him, not breaking eye contact until he mouthed softly at his neck once more, causing Cas to whimper softly. "Is this okay, Cas?" Dean asked against his neck, stopping until Cas spoke. 

"Don't s-stop," he replied, and Dean nodded. 

"I'll take care of you." 

Cas could feel his cold fingers travel all the way up to his chest, and he gasped when Dean touched his nipples. "Sensetive, hmm?" Dean hummed in his ear. "I'll be gentle. I promise." He lowered his hips and began grinding into Cas's thighs slowly. The clothing created unexpected friction and Cas gasped as he felt himself and Dean harden. He whimpered with anticipation. 

"Are-are we going to - " He couldn't bring himself to say it. 

Dean pulled back immediately, his eyes darkening while searching Castiel's face. "Only if you want." 

Cas hesitated, then looked down at the bulge in both of their pants. "I-I don't know why we're doing this, Dean. We're... F-friends. Right?" 

Dean's mouth stretched into a lopsided grin and he leaned closer on his elbows. "Can't friends do this, Cas?" He licked a thin stripe up Castiel's neck, causing him to shudder. "Also," he mumbled in his ear, "I think we've liked each other for a while now, hmm?" 

Cas bit his lip and nodded quickly, then wrapped his arms under Dean and around his back, clutching it tightly. "Keep going," he whispered, feeling his eyes begin to water with nervousness. "Just... G-go slow, Dean? I've never-I've never - " 

Dean brushed his lips against Cas's softly, shushing him. "I know, Cas. I know. I've got you." 

Slowly, Dean rose and gripped the bottom of his shirt, pulling it over his head. He hadn't realized how cold it was until now. "I'm going to take off your shirt now, alright?" 

Cas swallowed and nodded, shutting his eyes tightly. Soon his torso was exposed, and Dean's mouth explored all areas there, sucking lightly on his nipples, making him writhe against him. Dean grinded against Cas's hips, creating friction that made Cas cry out and open his eyes. "Oh, God, Dean," he whimpered beneath him, clinging onto his back for dear life. Jesus Christ, they hadn't even started yet and he was making a scene. 

"Shhh, you're okay," he whispered, pulling his wallet from his pants and taking out a small bottle of lube. Gradually he unbuckled his jeans and tossed them onto the floor, doing the same with Cas's. Cas bit his lip, trying to hold back all the obnoxious sounds he was about to make, and Dean seemed to notice. "C'mon Cas. I want to hear what I'm doing to you." Dean traveled down to his bulging cock, mouthing at the cloth.

Cas let out a long, broken moan, and gripped the blankets around him. "Oh my god Dean don't fucking stop," he cried out, babbling a bunch of nonsense he knew made him sound absolutely ridiculous. But he didn't care. He was being taken care of by Dean Winchester, his best friend, the boy he had crushed on since they were in diapers. He was going to be as loud as he wanted. 

"Okay, Cas, I'm gonna take off our boxers now, alright?" 

Cas nodded. 

Dean stripped himself, then reached behind Cas and tugged his down. "Lift," he commanded, and Cas obeyed, lifting his hips and getting rid of the underwear. He was embarrassed by all of this - nobody had seen him naked before. Not until now. He looked away as Dean stared at his throbbing cock. "God, Cas," he gasped quietly. "You're fucking perfect. You're beautiful." 

He uncapped the bottle, squirting a fair amount on his fingers before returning back to his original position, pecking him on the lips. "Cas, can you open your legs for me?" 

Cas sucked in a sharp breath, and spread them. 

"Okay, I'm going to start with one finger, alright?" He reached down. "You ever done this before, Cas? You ever finger yourself?" 

Castiel shook his head and tightly clutched Dean's back. "N-no," he said, and realized just how broken his voice was from all of this. "I h-haven't." 

Dean's cold finger circled his rim, making Cas tense in surprise. "It's okay, it's okay, Cas. I've got you. You're safe with me." After a few moments of soft pressure, Dean cleared his throat. "I'm gonna start, alright?" Cas couldn't bring himself to reply. He was so scared he felt tears threaten to spill. "Cas?" Dean stared into his eyes, a look of concern written on his face. "You gotta tell me how you're doing." 

Cas swallowed thickly and nodded. "I-I'm fine. You c-can start." 

Dean took a deep breath. "Okay." His finger slowly inserted Cas's hole, and Cas tensed up completely, his nails digging in Dean's back, feeling the burning sensation he had heard about. "Relax, baby, you're doing fine," Dean encouraged, kissing his jaw. "Breathe." 

Castiel inhaled sharply, a tear rolling down his cheek. "Just-just... G-give me a minute." 

Dean kissed his neck. "Of course," he whispered. "Tell me when you're ready." 

He didn't know if he was ever going to be ready. Sex was supposed to be enjoyable for both partners, but he knew that it was going to be hell for him. But he couldn't stop Dean. He couldn't disappoint him. After a moment or so, the burning died down a little. He took a deep breath and nodded. "You can move." 

Dean pumped his finger in and out, and Cas sighed in relief, holding him closely. He took it all back. It didn't hurt that bad. He could get used to it. "You can add another." 

Dean pulled away from his neck and looked deeply into his eyes. "Are you sure, Cas? I don't want to hurt you." 

Cas gave a small smile. "I trust you." 

And that was all Dean needed. He added another soon after, and Cas tried not to cringe at the burn. "Oh, God," he choked out, whimpering and tightening his grip on Dean. Dean kissed him slow and lovingly as he scissored into Cas deeply. "Oh, God, Dean." A tear rolled down his cheek. You can do this, Castiel. You're fine. "A-another," he croaked, after a few minutes when he was ready. Dean nodded, adding the last finger in, and Cas moaned when Dean brushed up against his sweet spot.  
"You like that, baby?" he whispered hoarsely into Castiel's ear. "How do you think my cock would feel?" 

Cas nearly screamed at the thought of it, but instead turned it into a low whimper. He already felt so full, he couldn't imagine what Dean would feel like inside of him. It was only a few moments later that Dean stopped scissoring his fingers and pecked Cas on the side of the mouth. "You ready?" 

Cas looked up. The TV screen was light enough to show Dean's bright green eyes staring back at him. They were really going to do this. "Yes," he said briefly. "Yes."

Dean rolled on a condom, slathering lube on his rock-hard dick, and then pressed the head against Cas's rim. Castiel clenched his eyes shut, holding onto Dean's back for dear life. "Cas, if I'm hurting you at all, you tell me, okay? I want this to be nice for both of us, not just me."

"I will," he whispered. He wrapped his legs around Dean's lower back.

And Dean began to push in. Castiel's eyes widened at the intense burn. He seemed much bigger than just three fingers. Tears rushed down his face as he continued to push in. "Oh God," he sobbed, his nails digging into Dean's back. "Oh God." His heels dug into his lower back.

"You're so tight, Cas," Dean whispered huskily in Cas's ear. "Are you doing okay?" 

The burn was slowly fading when Dean bottomed out, but Cas's tears didn't leave. They poured down his cheeks like a waterfall. "Oh God, Dean, oh God." His legs squeezed together. 

"You're okay, Cas, shhh," Dean soothed, and began peppering kissing down his neck and to his collarbone. "You're okay. God, I love you. I love you."  
Cas sobbed into Dean as Dean was buried into Cas's neck, biting and sucking and kissing. 

They stayed like that for a long time, until Cas adjusted to Dean's size. His breathing was rough and he couldn't calm his shot nerves. Dean was probably getting annoyed with him, he realized. Then Dean's face dragged up to Cas's, and he gave him a long, slow kiss, cupping his chin and then brushing his cheeks with his thumbs. "You can do this, Cas. I've got you, baby." 

They sat like that for a while longer, Dean panting softly and studying Castiel's face, and Castiel breathing heavily and trying to stop his tears. "I love you, you know that?" Dean stared into Cas's eyes, and when Cas looked away, he grabbed his face and pulled him back. "I want you to look at me, Castiel." He gave an experimental roll in his hips, causing Cas to scream, then release a sob that had been building up for a while. "I want you to know just how much I love you." Dean kissed the side of his mouth again. "You're beautiful, you know that?" 

Cas clutched Dean's back and closed his eyes. "Y-you can m-move," he hiccupped, gritting his teeth and preparing himself. 

Dean pecked his cheek, then buried his face in Castiel's neck. "I'll go slow, okay? I promise I will." 

Cas nodded, and then he began to move. It was slow, just as Dean had said it'd be. A small thrust. It didn't hurt as much as before, just a little sting, and Cas was glad. Then he realized just how gentle Dean was being, not even going fully in. "You c-can go deeper, Dean. I won't break." 

Dean let out a deep breath, almost sounding relieved. "Okay, Cas. I will." Dean sat up a little and gripped Cas's shoulders. "Just, hold onto my back, alright? We're gonna do fine." And he pulled his dick out of Cas, then shoved it back in, causing Cas to gasp and clutch Dean's back. Dean moaned as his grip tightened on Cas's shoulders, and he pumped himself in and out of Cas until he hit his sweet spot. 

Castiel cried out in pleasure and wrung his hands around Dean's neck, pulling him close. "Again," he breathed. 

Dean angled his hips, then rammed in once more, brushing up against Cas's prostate. He squeezed his eyes shut, feeling his orgasm build. "I'm not going to last long," he admitted, and Dean nodded eagerly.

"Me either," he whispered. "You're-" thrust "so-" thrust "tight," thrust. 

Cas whined as Dean dipped his lips to his face, kissing all the way from his forehead to his nose, then his cheeks and the corners of his mouth. He sucked in Cas's bottom lip, biting it softly, and Cas writhed beneath, whimpering against him. 

Dean pulled away, thrust, then buried his face into his neck. "God, Cas," he almost sobbed. "You're so perfect, you're so -" thrust "I'm gonna cum, I'm gonna cum, Cas." He desperately gripped Castiel's dick, pumping it as quickly as he could before the both of them spilled in unison. 

Cas's stomach was covered, and Dean slowly pulled out of him, making Cas whine softly. He would definitely be feeling this for a while. He threw out the condom, grabbing a wet handtowel on the way, then wiped them both up, making Cas shiver against the cool cloth. Once they were both clean, he then laid on top of Cas again, his face buried in his neck, just breathing him in. 

Cas's hands found their way into the back Dean's hair, and he tangled and twirled it with his fingers. Dean sighed tiredly against him, resting his arms by his sides and closing his eyes. 

Before he drifted into a deep sleep, Cas whispered into his ear, "I think I love you." 

Dean smiled against him. "I love you too, angel."

**Author's Note:**

> WOO!  
> Thanks for reading, guys!  
> I'm a little rusty on writing smut, but I hope it wasn't too terrible.  
> Have a nice night/day!


End file.
